5,7-dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one

• ChemBase编号: 105757
• 分子式: C16H12O5
• 平均质量: 284.26348
• 单一同位素质量: 284.06847348
• SMILES: COc1ccc(cc1)c1cc(=O)c2c(o1)cc(O)cc2O
• Canonical SMILES: COc1ccc(cc1)c1cc(=O)c2c(o1)cc(cc2O)O
• InChI: InChI=1S/C16H12O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-8,17-18H,1H3
• InChIKey: DANYIYRPLHHOCZ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5,7-dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one
• IUPAC传统名: acacetin
• 别名: 5,7-DIHYDROXY-4'-METHOXY FLAVONE; 5,7-dihydroxy-4′-methoxyflavone; 4'-methoxy-5,7-dihydroxyflavone; Linarigenin; Acacetine; Buddleoflavonol; Linarisenin; 4'-Methoxyapigenin; Apigenin 4'-methyl ether; 5,7-Dioxy-4'-methoxyflavone; 5,7-Dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one; 5,7-Dihydroxy-4'-methoxyflavone; ACACETIN; Acacetin; 2-(4-Methoxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one; 4'-O-Methylapigenin; LY 064233; NSC 76061

登记号

• CAS号: 480-44-4
• EC号: 207-552-3
• MDL号: MFCD00016936
• Beilstein号: 277879
• PubChem SID: 162092578
• PubChem CID: 5280442
• CHEBI ID: 15335
• CHEMBL: 243664
• Chemspider ID: 4444099
• 维基百科标题: Acacetin

理论计算性质

• Acid pKa: 6.577781
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): 2.8179076
• LogD (pH = 7.4): 1.9315174
• Log P: 2.8525832
• 摩尔折射率: 77.3962 cm^3
• 极化性: 29.011778 Å^3
• 极化表面积: 75.99 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO
• 外观: Pale Yellow Solid; Yellow powder
• 熔点: 260-265 °C(lit.); 262-264°C (dec.); 263°C

安全信息

• 保存条件: -20°C Freezer; Room Temperature (15-30°C)
• RTECS编号: DJ3002000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

详细说明

MP Biomedicals - 02193972

Possesses antioxidant properties and an inhibitor of rat liver glutathione S-transferase.

MP Biomedicals - 05212415

MP Biomedicals Rare Chemical collection

Sigma Aldrich - A8206

Biochem/physiol Actions
A flavonoid derivative possessing antioxidant properties.2 Induces cell cycle arrest and apoptosis in a time- and dose-dependent manner in several cancer cell lines in vitro.
Flavonoid with anti-peroxidative and anti-inflammatory properties. Used in traditional Chinese medicine. It has been recognized as an antiproliferative agent on cancer cell lines by inducing apoptosis and blocking cell cycle progression in the G1 phase.1

Toronto Research Chemicals - A123580

VEGF expression inhibitor and tumor angiogenesis. A flavonoid with antiaggregatory activity in human blood.

参考文献

• Zhang, K. and Das, N.P., Biochem. Pharmacol. , 47 : 2063 (1994).
• Liu, L. et al.: Biochem. Bioph. Res. Co. 413, 299 (2011)
• Bojic, M. et al.: Nutrition J. 10, 73 (2011)